Winthrop Vacation Packages

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    Save up to CA $775 when you book a flight and hotel together*
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Your Winthrop Vacation

There's no better way to escape than with one of our vacation packages to Winthrop. The rich history and coastal scenery are a couple of the countless reasons to visit this captivating city. Fill your free time with tours of Boston Common, Faneuil Hall Marketplace and Copley Place, some of the top attractions you simply have to see during your trip to Winthrop. Check out Expedia's extensive range of travel options and start planning your ideal vacation to Winthrop now.

Top Winthrop Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Aug. 25 - Aug. 28
found 15 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (2,257 reviews)
Everything was nice.

Reviewed on Jun. 11, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Jul. 31 - Aug. 4
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
Absolutely wonderful!

Reviewed on Jun. 11, 2024

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Aug. 24 - Aug. 27
found 15 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
What a treat it was stay at this hotel. Besides the fact it is absolutely stunning with great attention to detail, the staff was also fantastic, from the valet, to the doormen to front desk and cleaning service. Special shout out to Thomas from front desk who we dealt with for our stay. Made sure to have a room ready for us for early check in and always made sure we had everything we needed. We had a 10 month old, they had a crib ready for us which was a life saver. Location was also fantastic. All in all a 10/10 across the board and we cannot wait to stay there again.

Reviewed on Jun. 12, 2024

Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
Bay Village
Save 100% on your flight
per person
Jul. 31 - Aug. 4
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
8.4/10 Very Good! (3,336 reviews)
I like the hotel a lot.

Reviewed on Jun. 14, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug. 26 - Aug. 29
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (275 reviews)
EVERYTHING is thought out. Service is “old world”. Attention to details is magnificent. What’s there not to like.

Reviewed on Jun. 9, 2024

Winthrop Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4.5 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $283 per night from Jul. 3 to Jul. 4
CA $283
CA $370 total
includes taxes & fees
Jul 3 - Jul 4
9/10 Wonderful! (2,172 reviews)
"Nice property and amenities. Strange that guests need to "reserve" time at the pool. It also seemed strange that there was no pool access for guests in the morning they were checking out. Nice workout facility. Treadmills face a glass wall so if you're running in the morning on a sunny day bring ..."

Reviewed on Jun. 13, 2024

Omni Boston Hotel at the Seaport
Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $251 per night from Jul. 4 to Jul. 5
CA $251
CA $340 total
includes taxes & fees
Jul 4 - Jul 5
8.8/10 Excellent! (2,687 reviews)
"Everything was great!"

Reviewed on Jun. 10, 2024

Omni Parker House
The Revolution Hotel
The Revolution Hotel
3.5 out of 5
40 Berkeley Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $251 per night from Jun. 16 to Jun. 17
CA $251
CA $293 total
includes taxes & fees
Jun 16 - Jun 17
8.6/10 Excellent! (1,531 reviews)
"It’s renovated beautifully quite and clean."

Reviewed on Jun. 11, 2024

The Revolution Hotel
See all 3,269 properties in Winthrop
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Winthrop vacation package cost?
Starting from an incredible CA $859, you can tailor make your Winthrop vacation package. Simply combine hotels, flights and rental cars and be rewarded with discounts.
How do I get a cheap travel package to Winthrop?
Browse and book everything in one place with our Winthrop vacation packages. We have deals on flights, hotels and more that’ll keep your credit card happy and your adventurous spirit alive. And, with more than 550 airlines and 1,000,000 hotels worldwide to select from, you’ll have the flexibility to mix and match however you please.
Where should I stay in Winthrop?
You’ll want to stay where the action is. Many travelers favor hotels within easy reach of top attractions, like Revere Beach, Revere Beach Reservation and Winthrop Beach.
What are the top hotels in Winthrop?
Château Sur Mer Bed And Breakfast and Casa De Los Clarey Boston Airport Beaches Off Street Parking Available are among the most well-known hotels in Winthrop. Why not look up the amenities and rates at each and then make a decision?
How far in advance should I book my Winthrop vacation?
It’s hard to pick the perfect time for airfares, but we generally suggest the earlier, the better. Most international journeys on Expedia become available to compare up to a year in advance. If you’re booking last minute, don’t worry. Bargain prices occasionally appear within a few weeks of departure dates.
What does an Expedia Winthrop travel package include?
Expedia has all you need to book your Winthrop escape, but how you structure your package is your call. Select from any combination of flights, rental cars and hotels. Looking for some activities or tours to fill in your time? Once you’ve made your booking, you can add them on too. Whatever your budget, there’s a package deal to suit your needs.
What should I know before booking a Winthrop travel package?
Discover deals that match your budget with an Expedia package. Airfares, hotels, rental cars — we’ve got all of them. You’ll save big dollars just for combining your bookings. Whether you’re heading away on a ski adventure or venturing someplace warm, your ideal getaway is only a few clicks away.
Can I choose my airline with a Winthrop Expedia vacation package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines globally. Our packages give you the freedom to pick from available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Winthrop vacation package?
It’s hard to predict what tomorrow might bring, so it’s good to know that you can change or cancel your Winthrop vacation package. If your booking was made in the last 24 hours, you may be entitled to a refund. If it’s an older booking, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

Discover the most popular places to visit in Winthrop

Image for Fenway Park

Fenway Park

4.5/5(305 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Image for Harvard University

Harvard University

4.5/5(279 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Image for Gillette Stadium

Gillette Stadium

4.5/5(27 reviews)

Catch an event at Gillette Stadium during your trip to Foxboro. Experience the area's acclaimed theater scene and great live music.

Gillette Stadium

What to do in Winthrop

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $107
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Image for Bewitched Walking Tour of Salem

Bewitched Walking Tour of Salem

CA $41
Per adult
98% of travellers recommend
Bewitched Walking Tour of Salem
Image for Odyssey Boston Premier Elegant Dinner Cruise

Odyssey Boston Premier Elegant Dinner Cruise

CA $294
Per adult
Odyssey Boston Premier Elegant Dinner Cruise
See all activities in Winthrop
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.